15 Caribbean Islands That Are Perfect for Fall Getaways

By: - October 7th, 2025
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st barth villas
Maison Saline has a sparkling pool.

St Barth

St Barth in the fall is culinary heaven. The island prepares for its famous Gourmet Festival in November, when Michelin-starred chefs descend to collaborate with local talent in a weeklong celebration of food and wine. The beaches are serene, the water is warm and crystalline, and the atmosphere carries a quiet elegance — the calm before the high season, when those who know arrive early to enjoy the island at its most relaxed. There’s also the Caribbean Rum Awards Nov. 10-16.

Where to Stay
Les Îlets de la Plage is understated and elegant, tucked along a beautiful stretch of sand with villas that feel like private homes, perfect for travelers who want independence with subtle luxury. Le Barthélemy Hotel & Spa epitomizes polished Caribbean refinement, blending thoughtful design, exceptional service and a tranquil beachfront setting. Guanahani & Spa is a St Barth icon, where vibrant gardens, stylish rooms and warm hospitality create a resort experience that’s both sophisticated and deeply welcoming.

How to Get There
The best way is to fly to San Juan and then take Tradewind Aviation to St Barth. 

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About the author

Guy Britton is the managing editor of Caribbean Journal. With more than four decades of experience traveling the Caribbean, he is one of the world's foremost experts covering the region.
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